synthesis, crystal structure, and conformation of methyl 5-oacetyl-5-cyano-6-deoxy-2,3-o-isopropylidene-β-l-gulofuranoside的合成、晶体结构和构象甲基5-oacetyl-5-cyano-6-deoxy-2,3-o-isopropylidene-β-l-gulofuranoside.pdf

Molecules 2002, 7, 437–446 molecules ISSN 1420-3049 Synthesis, Crystal Structure, and Conformation of Methyl 5-O- acetyl-5-cyano-6-deoxy-2,3-O-isopropylidene-β-L-gulofuranoside 1 1 1 1 2 Júlia Mičová , Bohumil Steiner , Miroslav Koóš *, Ján Gajdoš , Vratislav Langer , and Dalma Gyepesová3 1 Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84238 Bratislava, Slovakia. Tel. (421)-2 Fax (421)-2 2 Department of Inorganic Environmental Chemistry, Chalmers University of Technology, SE-41296 Göteborg, Sweden 3 Institute of Inorganic Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-84236 Bratislava, Slovakia * Author to whom correspondence should be addressed; E-mail: chemmiro@savba.sk Received: 14 November 2001 / in revised form 13 May 2002 / Accepted: 13 May 2002 / Published: 31 May 2002 Abstract: Methyl 5-O-acetyl-5-cyano-6-deoxy-2,3-O-isopropylidene-β-L-gulofuranoside was prepared in high yield from methyl 6-deoxy-2,3-O-isopropylidene-α-D-lyxo- pentodialdo-1,4-furanoside. The configuration at the C5 atom was unambiguosly established by single crystal X-ray analysis of the corresponding 5-O-acetyl derivative. The conformation of the furanose and 1,3-dioxolane rings is also discussed. Keywords: Saccharide cyanohydrins, methyl 2,3-O-isopropylidene-β-L-gulofuranoside, X- ray crystallography, conformation. Molecules 2002, 7 438 Introduction In th